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Chemical Constituents and Pharmacology of the Aristolochia ( 馬兜鈴 Mădōu Ling) Species

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Chemical Constituents and Pharmacology of the Aristolochia ( 馬兜鈴 Mădōu Ling) Species View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Elsevier - Publisher Connector Journal of Traditional and Complementary Medicine Vol. 2, No. 4, pp. 249-266 Copyright © 2011 Committee on Chinese Medicine and Pharmacy, Taiwan. This is an open access article under the CC BY-NC-ND license. :ŽƵƌŶĂůŽĨdƌĂĚŝƚŝŽŶĂůĂŶĚŽŵƉůĞŵĞŶƚĂƌLJDĞĚŝĐŝŶĞ Journal homepagĞŚƩƉ͗ͬͬǁǁǁ͘ũƚĐŵ͘Žƌg Chemical Constituents and Pharmacology of the Aristolochia ( 馬兜鈴 mădōu ling) species Ping-Chung Kuo1, Yue-Chiun Li1, Tian-Shung Wu2,3,4,* 1 Department of Biotechnology, National Formosa University, Yunlin 632, Taiwan, ROC 2 Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan, ROC 3 Department of Pharmacy, China Medical University, Taichung 404, Taiwan, ROC 4 Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 404, Taiwan, ROC Abstract Aristolochia (馬兜鈴 mǎ dōu ling) is an important genus widely cultivated and had long been known for their extensive use in traditional Chinese medicine. The genus has attracted so much great interest because of their numerous biological activity reports and unique constituents, aristolochic acids (AAs). In 2004, we reviewed the metabolites of Aristolochia species which have appeared in the literature, concerning the isolation, structural elucidation, biological activity and literature references. In addition, the nephrotoxicity of aristolochic acids, biosynthetic studies, ecological adaptation, and chemotaxonomy researches were also covered in the past review. In the present manuscript, we wish to review the various physiologically active compounds of different classes reported from Aristolochia species in the period between 2004 and 2011. In regard to the chemical and biological aspects of the constituents from the Aristolochia genus, this review would address the continuous development in the phytochemistry and the therapeutic application of the Aristolochia species. Moreover, the recent nephrotoxicity studies related to aristolochic acids would be covered in this review and the structure-toxicity relationship would be discussed. Key words: Aristolochia, Aristolochic acid, Alkaloid, Flavonoid, Terpenoid, Bioactivity Introduction were widely distributed in tropical, subtropical and temperate regions of the world. They are known to There are about 500 species in the genus Aristolochia occur in Asia, Africa, North and South America and and the majority of these species are distributed in the Australia but there is a wide distribution across tropical tropical region, with some exceptions range as north Asia (Liu and Lai, 1976; How, 1985; Hou, 1996). as Canada, Scandinavia, and Northern Japan. They may grow as climbing vines, as short creeping herbs Various species of Aristolochia have been used in the and a few are shrub-like (Hutchinson, 1973; Watson folk and traditional medicines as medicaments and and Dallwitz, 1992; Gonzalez, 1999). Aristolochia tonics (Andrei, 1977; Correa, 1978; Balbach, 1979; species are herbaceous perennials, undershrubs or Duke, 1985; Duke and Ayensu, 1985; Simoes et al, shrubs, often scandent, scrambling, twining, sometimes 1986; Lopes et al, 2001), especially in the traditional lianas, usually with prostrate or tuberous rhizomes or Chinese medicines (Jiangsu New Medicine College, rootstocks, and alternate, pinnate, polymorphic or lobed 1977; Li, 1977; Pharmacopeia of China, 1985; Tang leaves bearing essential oils. Species of Aristolochia and Eisenbrand, 1992; Bensky, 1993). Some species *Correspondence to: Dr. Tian-Shung Wu. Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan, ROC, Tel: 886-6-2757575 ext 65333, Fax: 886-6-2740552, E-mail: [email protected] 249 Kuo et al. / Journal of Traditional and Complementary Medicine 2 (2012) 249-266 have been used in the form of crude drugs as anodynes, Chemical Constituents antiphlogistics, and detoxicants in Mainland China In the period between 2004 and 2011 over eighteen (Perry, 1980). In our previous review article (Wu et al, species of Aristolochia have been investigated for 2005), the purification, structural elucidation, and the chemical constituents around the world, and various biological activity of metabolites of Aristolochia species constituents have been characterized (Table 1). The have been covered and moreover the nephrotoxicity secondary metabolites from Aristolochia species cover of aristolochic acids, biosynthetic studies, ecological 16 major groups classified by their chemical structures, adaptation, and chemotaxonomy researches were also including aristolochic acids and esters, aristolactams, cited. In this present manuscript, we aimed to address aporphines, protoberberines, isoquinolines, the continuous development regarding the presences benzylisoquinolines, amides, flavonoids, lignans, of the various metabolites identified from Aristolochia biphenyl ethers, coumarins, tetralones, terpenoids, species and also their divergent bioactivities. benzenoids, steroids, and others. The aristolochic acids were host of phenanthrene derived metabolites in which the aristolactams also possessed the similar skeleton. The identified terpenoids can further be divided into three subgroups: mono-, sesqui-, and diterpenoids. Table 1. Chemical constituents from the Aristolochia (馬兜鈴 mǎ dōu ling) species. Species Part Compound Reference A. species aristolochic acid I; aristolochic acid A (1) Chen et al, 2010a A. albida whole plant columbin (2) Nok et al, 2005 A. arcuata roots talaumidin (3) Zhai et al, 2004 Zhai et al, 2005 veraguensin (4) Zhai et al, 2005 galgravin (5) aristolignin (6) nectandrin A (7) isonectandrin B (8) nectandrin B (9) A. brevipes ground roots β-sitosterol (10) Navarro-García et al, 2011 6α-7-dehydro-N-formyl-nornantenine (11) E/Z-N-formylnornantenine (12) 7,9-dimethoxytariacuripyrone (13) 9-methoxytariacuripyrone (14) aristololactam I (15) stigmasterol (16) 3-hydroxy-α-terpineol (17) A. constricta stems aristolochic acid A (1) Zhang et al, 2008 (18) Capasso et al, 2006 (19) (20) (21) (22) (23) stems (−)-hinokinin (24) Zhang et al, 2008 9-O-[(−)-kaur-15-en-17-oxyl]cubebin (25) (−)-cubebin (26) (−)-kaur-15-en-17-ol (27) (−)-pluviatolide (28) (−)-haplomyrfolol (29) (−)-dihydrocubebin (30) 9-O-methylcubebin (31) (−)-kaur-16-en-19-oic acid (32) (−)-kauran-16α,17-diol (33) 250 Kuo et al. / Journal of Traditional and Complementary Medicine 2 (2012) 249-266 Species Part Compound Reference (−)-kaurene (34) (−)-kauran-16α,17,18-triol (35) aristololactam AII; aristolactam AII (36) cepharanone B (37) aristelegone A (38) (+)-4,7-dimethyl-6-methoxy-1-tetralone (39) cadalene (40) β-sitosterol glucoside; β-sitosteryl glucoside (41) N-trans-feruloyltyramine (42) A. contorta fruits 3"-hydroxyamentoflavone-7-O-methyl ether (43) Chen et al, 2005 3"-hydroxyamentoflavone (44) A. cretica roots aristolochic acid I; aristolochic acid A (1) Georgopoulou et al, 2005 aristolochic acid IIIa; aristolochic acid C (45) 6-O-p-coumaroyl-β-D-fructofuranosyl-(2→1)-α-D- glucopyranoside (46) arillatose B (47) 6-O-p-coumaroyl-α-D-glucopyranose (48) 6-O-p-coumaroyl-β-D-glucopyranose (49) 7-hydroxyaristolochic acid I (50) aristolochic acid II; aristolochic acid B (51) ariskanin A (52) A. cymbifera whole plant 2-oxo-populifolic acid (53) de Barros Machado et al, 2005 leaves (−)-hinokinin (24) Sartorelli et al, 2010 (−)-kusunokinin (54) (−)-copalic acid (55) (−)-fargesin (56) (+)-sesamin (57) epieudesmin (58) A. elegans stems and roots aristolochic acid I; aristolochic acid A (1) Shi et al, 2004 β-sitosterol (10) (−)-hinokinin (24) (−)-cubebin (26) (−)-kaur-15-en-17-ol (27) aristolactam AII; aristololactam AII (36) aristelegone A (38) β-sitosteryl glucoside (41) N-trans-feruloyltyramine (42) N-trans-cinnamyltyramine(54) aristolactam E (59) aristolactam-AIIIa-6-O-β-D-glucoside (60) aristoquinoline A (61) aristoquinoline B (62) aristoquinoline C (63) aristogin F (64) 9-methoxyaristolactam I (65) isoaristolactam AII (66) aristolactam AIIIa (67) aristolactam C N-β-D-glucoside (68) aristogin A (69) aristogin B (70) aristogin C (71) aristogin D (72) aristogin E (73) 4-methoxy-3,4'-oxydibenzoic acid (74) aristelegone B (75) aristelegone C (76) aristelegone D (77) pericampylinone A (78) corydaldine (79) thalifoline (80) 251 Kuo et al. / Journal of Traditional and Complementary Medicine 2 (2012) 249-266 Species Part Compound Reference northalifoline (81) N-methylcorydaldine (82) aristelegin A (83) aristelegin B (84) aristelegin C (85) α-methylcubebin (86) β-methylcubebin (87) (−)-5"-methoxyhinokinin (88) (−)-kobusin (89) (+)-medioresinol (90) aristolin (91) ent-kauran-16β,17-diol (92) ent-16β,17-epoxykauran (93) ent-15β,16-epoxykauran-17-ol (94) aristololide (95) N-cis-feruloyltyramine (96) N-p-trans-coumaroyltyramine (97) aristolochic acid IVa; aristolochic acid D (98) aristoloside (99) aristolochic acid IV methyl ester (100) methyl aristolochate; aristolochic acid I methyl ester (101) aristolochic acid D methyl ester (102) aristolochic acid Ia methyl ester (103) magnofoline; magnoflorine (104) oxonuciforine (105) isomoschatoline (106) 4,5-dioxodehydroasimilobine (107) methylparaben (108) methyl vanillate (109) p-hydroxybenzaldehyde (110) vanillin (111) methyl 4-hydroxy-3-methoxycinnamate (112) cinnamic acid (113) ω-hydroxypropioguaiacone (114) ficusol (115) A. fangchi roots aristolochic acid A; aristolochic acid I (1) Cai and Cai, 2010 aristolochic acid C; aristolochic acid IIIa (45) aristolochic acid B; aristolochic acid II (51) aristolochic acid F
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